Jeffrey grew up in Courtright, Ontario, playing minor hockey for the Mooretown Flags and the Lambton Jr. Sting AAA teams of the Pavilion League.

His season came to an end on March 24, 2011, when he was placed on the injured reserve due to a "lower body injury" after Philadelphia Flyers forward Jeff Carter fell on Jeffrey's right knee.

[5] It was revealed on April 5, 2011 that he had a torn ACL and had undergone surgery; he required six months' worth of rehabilitation and did not return until the start of the 2011–12 season.

[7] On October 10, 2012, with the NHL lock-out in effect, Jeffrey signed a temporary contract with Croatian club KHL Medveščak Zagreb of the Austrian Hockey League.

[10] On July 1, 2015, Jeffrey continued his journeyman career in signing a one-year, two-way contract as a free agent with the Arizona Coyotes.

After scoring 46 points in just 45 games, Jeffrey was dealt by the Coyotes alongside Dan O'Donoghue and James Melindy in a return to the Pittsburgh Penguins organization in exchange for Matia Marcantuoni on February 29, 2016.

[12] On June 3, 2016, Jeffrey left North America and agreed to a two-year contract with Lausanne HC of the National League (NL).